Should you start watching anime or not?
The more genres or options you consider, the better; it broadens your horizons and gives you more to choose from.
If you want something philosophical, Nebok, check out "Kino no Tabi." I always praise it.
If you want something philosophical with a touch of absurdity, then "Spirited Away" might be a good option. Well, if you haven't seen it yet.
In general, I'm not an anime expert, but I can name a few works that I like.